461326

Sigma-Aldrich

Melatonin

≥99.5%

Synonym(s):
N-Acetyl-5-methoxytryptamine
Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
Molecular Weight:
232.28
Beilstein/REAXYS Number:
205542
EC Number:
MDL number:
PubChem Substance ID:

assay

≥99.5%

form

powder

mp

116.5-118 °C (lit.)

SMILES string

COc1ccc2[nH]cc(CCNC(C)=O)c2c1

InChI

1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)

InChI key

DRLFMBDRBRZALE-UHFFFAOYSA-N

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Certificate of Analysis

Certificate of Origin

Paul P Drury et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 34(1), 126-135 (2013-10-10)
Melatonin is a naturally occurring indolamine with mild antioxidant properties that is neuroprotective in perinatal animals. There is limited information on its effects on preterm brain injury. In this study, 23 chronically instrumented fetal sheep received 25 minutes of complete umbilical...
L P H Andersen et al.
Anaesthesia, 69(10), 1163-1171 (2014-05-20)
We systematically reviewed randomised controlled trials of peri-operative melatonin. We included 24 studies of 1794 participants that reported eight peri-operative outcomes: anxiety; analgesia; sleep quality; oxidative stress; emergence behaviour; anaesthetic requirements; steal induction; and safety. Compared with placebo, melatonin reduced...
Juan R Calvo et al.
Journal of pineal research, 55(2), 103-120 (2013-07-31)
Melatonin is the major secretory product synthesized and secreted by the pineal gland and shows both a wide distribution within phylogenetically distant organisms from bacteria to humans and a great functional versatility. In recent years, a considerable amount of experimental...
Reuben K Wong et al.
Digestive diseases and sciences, 60(1), 186-194 (2014-08-06)
Probiotics have treatment efficacy in irritable bowel syndrome (IBS), but the exact mechanism remains obscure. One hypothesis is the mediation of melatonin levels, leading to changes in IBS symptoms. The purpose of this study was to evaluate the effects of...
Valérie Biran et al.
Developmental medicine and child neurology, 56(8), 717-723 (2014-03-01)
The prevention of neurological disabilities following preterm birth remains a major public health challenge and efforts are still needed to test the neuroprotective properties of candidate molecules. Melatonin serves as a neuroprotectant in adult models of cerebral ischemia through its...

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